Stereoselective synthesis of (2S,3S,4Z)-4-fluoro-1,3-dihydroxy-2- (octadecanoylamino) octadec-4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface

Abstract

Sphingolipids belong to the most important constituents of the membranes of eukaryotic cells. As intermediates in sphingolipid metabolism, sphingosine and its N-octadecanoyl-derivative, ceramide, exhibit a variety of biological functions. These compounds play a crucial role in many essential biological processes such as cell growth, cell differentiation, cell recognition and apoptosis. More specifically, sphingolipids are crucial e.g. for the function of the skin because they contribute to the formation of the water permeability barrier consisting of a highly organized multilaminar lipid matrix of free fatty acids, cholesterol and ceramides containing additional hydroxyl groups in the sphingosin part and longer fatty acid amide functions. © 2008 Nikolova and Haufe; licensee Beilstein-Institut.